Has anyone used Free File Fillable Forms to handle this? I'm trying to do my own taxes with backdoor Roth for the first time and I'm completely lost on how to properly report everything.

I went through this exact same situation last year and want to share what I learned! You're absolutely right to be concerned - taking the deduction when doing a Backdoor Roth creates a tax mess. Here's what happened in your case: You deducted the Traditional IRA contribution (getting a tax benefit now), but then converted that pre-tax money to a Roth IRA. The IRS sees this conversion as taxable income since you're moving pre-tax dollars into an after-tax account. If you didn't report the conversion as income on your return, you definitely need to amend. You have two paths forward: 1. Keep the deduction and add the conversion as taxable income on an amended return 2. Remove the deduction, file Form 8606 for a non-deductible contribution, and the conversion won't be taxable For future reference, the classic Backdoor Roth strategy uses option 2 - make non-deductible contributions specifically so the conversion isn't a taxable event. Since you were eligible for the deduction (no employer plan), you had to actively choose NOT to take it. I'd recommend consulting with a tax professional before amending, as they can run the numbers to see which option saves you more in taxes. The timing matters too since amended returns take months to process.

Just FYI for anyone dealing with tax equalization - make SURE you understand how they're calculating your hypothetical tax. Some companies use a really simplified formula that doesn't account for all the deductions and credits you might normally claim. Also, watch out for state taxes in the calculation. If you've established residency overseas and cut ties with your home state, you shouldn't be paying state hypo tax, but some companies still include it.

This is exactly why I wish I had known about these issues before my company implemented their tax equalization program. I ended up losing about $15K annually in tax benefits that I was getting from FEIE, and the company basically pockets that difference since I'm in a low-tax jurisdiction. One thing I learned the hard way - READ THE FINE PRINT on your tax equalization agreement. Mine had a clause that said any "windfalls" (including FEIE benefits) go back to the company. I had no idea what I was signing at the time. If you're still in the negotiation phase, try to get them to at least give you a detailed breakdown of how your specific situation will be affected. Don't just accept their generic "you'll be tax neutral" explanation - demand to see the actual numbers based on your last few years of returns. Also, document everything about your current tax situation now while you still can file independently. If you ever leave the company or they change the policy, you'll want that baseline to return to normal filing.

My tax person told me that for 2024, the rules are different if the total estate was over $13.61 million. Was your dad's estate really big beyond just the house? If it was over that amount, there might be estate taxes to consider, but most people don't hit that threshold.

Just want to add one important detail that might help - make sure you keep good records of the property appraisal that was done after your dad's death. That appraisal establishing the $285,000 value is what determines your stepped-up basis, and you'll want to have that documentation if the IRS ever questions your return. Also, since you mentioned this happened "last year," make sure the date of death and date of sale are both clearly documented on your Schedule D. The IRS likes to see that timeline to confirm you're handling inherited property correctly. If there was any time gap between when your dad passed and when the appraisal was done, you might want to note that as well. Sounds like you're on the right track with reporting zero gain - just make sure your paperwork is solid to back it up!

Dont forget to factor in legal protections too not just taxes! Having LLC own C-Corp creates an extra layer between u and liabilities which can be good. But also makes raising more $$ more complicated cause investors gotta go thru LLC to get to C-Corp. I had similar setup and ended up with C-Corp as parent instead, with an LLC subsidiary for riskier parts of business. made subsequent funding rounds WAY easier. just my 2 cents

This is a really complex area and I'd strongly recommend getting professional advice, but I can share some insights from my experience with similar structures. One major consideration that hasn't been fully addressed is the potential Section 351 tax implications when you contribute assets from your LLC to the new C-Corp. If you're transferring property (including IP, equipment, or other business assets) from your LLC to the C-Corp in exchange for stock, you'll want to make sure this qualifies for tax-free treatment under Section 351. Otherwise, you could trigger immediate taxable gain recognition. Also, regarding the double taxation issue - while it's true that C-Corp dividends create double taxation, many startups avoid this by not paying dividends at all. Instead, they reinvest profits back into the business or compensate key employees (including yourself) through reasonable salaries and bonuses, which are deductible to the C-Corp. Another strategy to consider is having the LLC provide legitimate services to the C-Corp (as mentioned earlier) - things like administrative services, office space rental, or consulting. This creates a deductible expense for the C-Corp and income for the LLC, which can help optimize the overall tax burden. Just make sure all inter-company transactions are properly documented and at fair market value to avoid IRS scrutiny!

5 My restaurant does something weird where they add an "assumed cash tip" percentage to our reported income even when we honestly report everything. Is that legal??

Been serving for about 2 years now and wanted to share what I've learned about cash tip taxes since I was in the same confused boat when I started! Yes, when you report cash tips on your checkout form, those get added to your total taxable income for that pay period. Your employer should then withhold taxes on ALL your tips (cash + credit card) from your paycheck. This is why you'll sometimes see really small paychecks even after a good night - the taxes on your cash tips are being taken out of your credit card tip money. One thing that caught me off guard early on: if you have a really good cash night but low credit card tips, there might not be enough in your paycheck to cover all the tax withholding. When that happens, you'll owe the difference when you file your taxes in April. My advice is to set aside about 25-30% of your cash tips in a separate envelope or savings account, just in case. Better to have too much saved than get hit with a surprise tax bill! Also definitely keep your own daily tip log - don't just rely on what the restaurant tracks.